Ammonium Chloride → HCID 57551748, compound

HRID 907251Notes

Reaction equation

HRID 907251 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].C[O:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH3:46])=[C:13]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]4[CH2:34][CH2:35][N:36](C(OC(C)(C)C)=O)[CH2:37][CH:38]=4)=[CH:29][CH:28]=2)[CH:19]=[CH:18]3)[CH:14]=1)=O.C([Mg]Cl)(C)C.[Cl-].[NH4+]>C1COCC1>[CH3:3][O:2][NH:4][C:7](=[O:6])[C:9]1[CH:10]=[CH:11][C:12]([CH3:46])=[C:13]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[N:20]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]4[CH2:34][CH2:35][NH:36][CH2:37][CH:38]=4)=[CH:29][CH:28]=2)[CH:19]=[CH:18]3)[CH:14]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 57551773HCID 57551773, compoundHCID 178418918HCID 178418918, compound2×

Product 1

HCID 57551748HCID 57551748, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Methoxylamine hydrochloride (0.12 g) was added to a solution of Example 6 step (ii) (0.4 g) in THF (10 mL). The mixture was stirred at room temperature then 2.0M isopropylmagnesium chloride in THF (1 mL) added. The mixture was stirred for 1 hour then a further portion of 2.0M isopropylmagnesium chloride in THF (1 mL) was added. The mixture was stirred for a further 1 hour then poured into saturated aqueous ammonium chloride and extracted with dichloromethane. The organics were combined and evaporated under reduced pressure. The residue was dissolved in methanol (20 mL) and 2.0M HCl in diethyl ether added (20 mL). This solution was stirred at room temperature for 12 hours. The volatiles were removed under reduced pressure and the residue purified (SiO2 10:90:1 methanol:dichoromethane:aqueous ammonia as eluant) to give the title compound as a solid (22 mg).

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. stirringThe mixture was stirred for a further 1 hour
  3. extractionextracted with dichloromethane
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (20 mL)
  6. addition2.0M HCl in diethyl ether added (20 mL)
  7. stirringThis solution was stirred at room temperature for 12 hours
  8. customThe volatiles were removed under reduced pressure
  9. customthe residue purified (SiO2 10:90:1 methanol:dichoromethane:aqueous ammonia as eluant)

Sources & evidence

ORD record
ord-ce66a2a0b1cd42febdf389c6380484d3
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

Loading…